ES419927A2 - Cephalosporin derivatives - Google Patents

Cephalosporin derivatives

Info

Publication number
ES419927A2
ES419927A2 ES419927A ES419927A ES419927A2 ES 419927 A2 ES419927 A2 ES 419927A2 ES 419927 A ES419927 A ES 419927A ES 419927 A ES419927 A ES 419927A ES 419927 A2 ES419927 A2 ES 419927A2
Authority
ES
Spain
Prior art keywords
acylamido
group
cef
butoxyimino
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
ES419927A
Other languages
Spanish (es)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Publication of ES419927A2 publication Critical patent/ES419927A2/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

Improvements introduced in the object of the main patent No. 402,651 applied for on May 12, 1972 for: "Procedure for the preparation of cephalosporin derivatives" according to which when said compounds are selected from the group consisting of: (a) 7β- acids acylamido-3-acetoxymethyl cef-3-em-4-carboxylic acids, wherein the acylamido group at position 7β is 2-aryloxyimino-2-phenylacelamido; 2-aryloxyimino-2-thienylacetamido; 2-aryloxyimino-2-furylacetamido; 2-cyclopentyloxyimino-2-phenylacelamido; 2-cyclopentyloxyimino-2-thienylacetamido; 2-cyclopentyloxyimino-2-furylacetamido; 2-t-butoxyimino-2- (benzo [b] furan-2-yl) acetamia; 2-methoxyimino-2- (N-methylpyrrol-2-yl) acetamido; 2-t-butoxyimino-2- (N-methylpyrrol-2-yl) acetamido; 2-thienylmethoxyimino-2- (N-methylpyrrol-2-yl) acetamido; 2-methoxyimino-2- (N-benzyloxymethylpyrrol-2-yl) acetamido; or 2-carboxymethoxyimino-2-phenylacetamido; the aryl part of said aryloxy group comprising phenyl, thienyl, furyl or phenyl substituted by one or more of chlorine, nitro, amino, carboxy and methoxy; (b) 7β-acylamido-3- (1-methyltetrazol-5-ylthiomethyl) cef-3-em-4-carboxylic acids and 7β-acylamido-3- (1-ethyltetrazol-5-thiomethyl) cef-3-em-4 acids -carboxylics in which the acylamido group in position 7β is a group of formula RC (: NORa) .CO- where R is selected from phenyl, thienyl, and furyl and Ra is selected from methyl, ethyl, t-butyl, cyclopentyl, phenyl, furylmethyl and triphenylmethyl; (c) 7β-acylamido-3- (5-nitrobenzothiazol-2-ylthiomethyl) cef-3-em-4-carboxylic acids and 7β-acylamido-3- (6-nitrobenzothiazol-2-ylthiomethyl) cef-3-em -4-carboxylic acids where the acylamido group in the 7β position is a group of formula RC (: NORa) .CO where R is selected from phenyl, thienyl and furyl and Ra is selected from t-butyl, cyclopentyl and phenyl; (d) 7β-acylamido-3-vinyl cef-3-em-4-carboxylic acids wherein the acylamido group at the 7β position is 2-t-butoxyimino-2-thienylacetamido; 2-ethoxyimino-2-phenylacetamido; or 2-t-butoxyimino-2- (benzo [b] thien-3-yl) acetamido; (e) 7β-acylamido-3-crotonyloxymethyl cef-3-em-4-carboxylic acids where the acylamido group at position 7β is 2-t-butoxyimino-2-thienylacetamido or 2-t-butoxyimino-2- (benzo [b ] -tien-3-yl) acetamido; (f) 7β- [2-t-butoxyimino-2-thienylacetamido] -3- (2-phenyl-1,3,4, -oxadiazol-5-ylthiomethyl) cef3-em-4-carboxylic acid; (g) 3-acetylthiomethyl-7β- (2-ethoxyimino-2-phenylacetamido) -cef-3-em-4-carboxylic acid; and non-toxic derivatives of these acids, said compound existing as an isomer without or a mixture of an isomer without such and the corresponding anti-isomer, where the configuration does not predominate, and which have the general formula **(See formula)** [where Ra and P have appropriate meanings corresponding to those encompassed by (a) - (g) above] said improvements comprise either (A) condensing a compound of formula **(See formula)** (where P has the meaning before indicated and R1 represents hydrogen or a carboxyl group blocking group) with an acylating agent corresponding to the acid Rα.OR (III) (Wherein, Rα has the meaning indicated above); or (b) reacting a compound of formula **(See formula)** (where Rα and R1 have the meanings indicated above and P1 is a precursor of the desired P-substituent), with a reagent or reagents serving to introduce said group P; and (C) recovering the desired compound of formula I, if necessary after separation of isomers and/or removal of any carboxyl group blocking groups and if desired after conversion of compound (I) into a non-toxic derivative. . (Machine-translation by Google Translate, not legally binding)
ES419927A 1972-10-25 1973-10-24 Cephalosporin derivatives Expired ES419927A2 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4925572A GB1445979A (en) 1972-10-25 1972-10-25 Cephalosporin derivatives

Publications (1)

Publication Number Publication Date
ES419927A2 true ES419927A2 (en) 1976-11-16

Family

ID=10451708

Family Applications (1)

Application Number Title Priority Date Filing Date
ES419927A Expired ES419927A2 (en) 1972-10-25 1973-10-24 Cephalosporin derivatives

Country Status (7)

Country Link
JP (1) JPS4972286A (en)
BE (1) BE806450R (en)
ES (1) ES419927A2 (en)
FR (1) FR2204403B2 (en)
GB (1) GB1445979A (en)
LU (1) LU68680A1 (en)
ZA (1) ZA738251B (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4095021A (en) 1973-12-21 1978-06-13 Glaxo Laboratories Limited 3-Carbamoyloxymethyl or N-methyl-carbamoyloxymethyl-7-[2-carboxymethoxyimino-2-(fur-2-yl or thien-2-yl)acetamido]ceph-3-em-4-carboxylic acids and derivatives thereof
US4144392A (en) 1973-12-21 1979-03-13 Glaxo Laboratories Limited Cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyimino-arylacetamido group and at position-3 the residue of a sulphur nucleophile
US4165430A (en) 1976-03-19 1979-08-21 Glaxo Laboratories Limited Cephalosporins having a 7-carboxy substituted α-etherified oximinoarylacetamido) group
GB1576625A (en) * 1976-04-12 1980-10-08 Fujisawa Pharmaceutical Co Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof
FI771866A (en) * 1976-06-28 1977-12-29 Fujisawa Pharmaceutical Co
GB1592149A (en) * 1976-10-08 1981-07-01 Fujisawa Pharmaceutical Co 3 7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for preparation thereof
US4409214A (en) * 1979-11-19 1983-10-11 Fujisawa Pharmaceutical, Co., Ltd. 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof
JPS5818388A (en) * 1981-07-28 1983-02-02 Banyu Pharmaceut Co Ltd Preparation of 3-substituted thiomethylcephalosporin derivative
US4492693A (en) * 1983-04-12 1985-01-08 Eli Lilly And Company Benzothienylglycyl cephalosporin derivatives
GB8927871D0 (en) * 1989-12-08 1990-02-14 Beecham Group Plc Novel compounds
CA2613303C (en) 2005-07-11 2012-06-19 Mitsubishi Tanabe Pharma Corporation An oxime derivative for use as a glucokinase activator
JP2008019241A (en) * 2007-03-01 2008-01-31 Mitsubishi Tanabe Pharma Corp Oxime derivative and method for producing the same
WO2018053587A1 (en) * 2016-09-21 2018-03-29 Vectus Biosystems Limited Compositions for the treatment of hypertension and/or fibrosis
FR3135420B1 (en) 2022-05-10 2024-03-29 Psa Automobiles Sa System for holding the end of a screw in a frame rail for a motor vehicle

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1399086A (en) * 1971-05-14 1975-06-25 Glaxo Lab Ltd Cephalosporin compounds

Also Published As

Publication number Publication date
FR2204403B2 (en) 1976-12-24
ZA738251B (en) 1974-10-30
FR2204403A2 (en) 1974-05-24
GB1445979A (en) 1976-08-11
BE806450R (en) 1974-04-24
LU68680A1 (en) 1974-01-08
JPS4972286A (en) 1974-07-12

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